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Times shown are "cast-off" times. Please arrive 30-45 minutes early.

For all event descriptions


For specific sail, select the events name below.

Lakeside Architecture
Real Pirates
It's a Sailor's Life for Me!
Spirit Ships & Haunted Harbors
5:45p"Whale Watching" - Every Friday
Skyline Sail
Captain's Choice
9:15pm Wednesday Fireworks
9:15pm Saturday Fireworks

Sailing options:

Weddings and Wedding Parties

Field Trips


Educational Adventures


City of Chicago Resolution

Rates for Schooner Windy Events:

  1. Private Charters
  2. Group Rates
  3. Ticketing Rates and info
  4. Concession and Bar info

RATES For Private Charters

Charters are limited to 150 passengers. All charters will be under contract.
Call 312-451-2700 for reservations.
Charters are confirmed when deposit/payment has been received.

A 25% deposit will confirm charters with the balance due 4 weeks before sailing. Cash or Checks are preferred. Most Credit Cards are accepted, a 3.25% fee may apply.

Rates will be higher during special events. These rates are subject to change.

Charter start times are be the same as our published schedule.

Length: Mon - Tues Wed - Fri Sat - Sun Fireworks
60 min $2145.00 $2295.00 $3095.00 -
75 min $2681.00 $2868.00 $3126.00 $4795.00
2.5 hrs $4826.00 $5173.00 $6963.00 2hr $7195.00
2.75 hrs $5898.00 $6311.00 $8511.00 2hr $7195.00

All Charters are plus 12% tax. Crew gratuity of 10% will be added to charters. Charters on special event dates, will be more.

CANCELLATIONS: Charters can be cancelled for a partial refund. A five percent (5%) processing charge will be applied if charter is cancelled more than 4 weeks before sailing date. Every effort will be made to reschedule a postponed charter, at no charge. If your group cannot reschedule: Cancellations 2-4 weeks before the charter date, will be charged 15% cancellation fee. Charters cancelled two weeks- 72 hours before the event will be charged 40%. Cancellations less than 72 hours before the event will be charged in full. If the Captain cancels for any reason, unforeseen circumstances or inclement weather, a full refund is given.

If Captain cancels for inappropriate or illegal behavior by the charterer or their guests, no refunds will be given.

WEATHER: It is our sincere desire is that you have a pleasant experience aboard, and we will do our best to have your charter proceed as planned on that day.

Cancellations due to weather will be at the Captain's discretion. Inclement weather is defined as cold or stormy conditions which exceed the average passing summer shower, and require more than a season-appropriate jacket. The charter leader will be notified within 2 hours of the charter if there is a threat of weather cancellation if possible. Very few charters are cancelled due to weather, and it is possible to set up a drizzle proof tarp on the main deck in case of a passing shower.


For groups of fewer than 20 guests, please make reservations online, or purchase your tickets at the booth on the day of your visit. For groups of 20 or more, you may call us at 312-451-2700 to make reservations in advance.

Number of guests: DISCOUNTS:
20-39 persons 10% discount
40-60 15% discount
60+ 20% discount

To make group RESERVATIONS: It is best to call and make advance reservations. Groups are considered confirmed when the tickets are purchased. They are only partially refundable. Tax exemption may not be applied, since the tax applied to Windy tickets is an Amusement tax levied by the City of Chicago and Cook County. Cash, Checks, Master Card and VISA are accepted.
NO SHOWS & LAST MINUTE ADDITIONS: If you are unsure of your head count, please under-book as refunds are not given for NO SHOWS. Those who cannot commit in advance will be walk-ons on the day of sail paying full regular fare. On a space available basis, walk-ons can usually be called in by the group leader and space held until 30 minutes before sailing. There are no guarantees for walk-ons within 30 minutes of sailing.


No refunds for pre-paid group tickets. Groups who must cancel will be offered a chance to reschedule at a future date, with no additional charge if 24-hour notice is given. Pre-paid groups are considered ticket purchases and have the same cancellation and refund policies applied to them. They are subject to a 2-hour postponement without refund, please plan accordingly. Windy is a rain or shine vessel.

Refunds are not given for NO SHOWS, as it is a privilege to book reservations on Public Sails. Refunds if any, will be given in Gift Certificate form. If the Captain cancels for any reason, unforeseen circumstances or severe weather, a full refund will be provided.

WEATHER: Postponements and cancellations due to weather will be at the Captain's discretion that day, sails may be postponed up to 2 hours. Sailing on Windy is a rain or shine event.

BOARDING PASSES: Passes can be mailed if time allows. Most group leaders pick them up upon arrival to Navy Pier that day. Groups are boarded along with other public passengers a few minutes before sail time.

Please note that WINDY is NOT "Handicapped Accessible" as it is considered an adventure activity. Access to the main deck is six stairs with hand rails (sometimes the ship is moving from waves), no ramps are available.